Van Heemskerck was a painter from Haarlem who worked in England from about 1675 until his death. He specialised in a kind of subject matter common in the Netherlands but new to English painting: depictions of groups of ordinary people in comic or vulgar situations, including rowdy tavern scenes, Quaker meetings and school classrooms. He worked at the court of Charles II. He may have been patronised by the extravagant courtier, John Wilmot, 2nd Earl of Rochester. According to contemporary critics his work also found a flourishing market among 'the waggish collectors and the lower rank of virtuosi'.
The painting he holds in this portrait is typical of his work. With his slightly wild appearance, Van Heemskerck himself is shown as the sort of person who might appear in one of his paintings.